In eighth grade, Schlossberg co-founded ReLight New York, a non-profit organization that raised more than $100,000 to install compact fluorescent lights in low-income housing developments.[2] In 2011, he graduated as class valedictorian from Collegiate on the Upper West Side of Manhattan.[7]

In October 2015, after graduating from Yale, Schlossberg started working at Rakuten, Inc, a Japanese internet and e-commerce company, in Tokyo, Japan. He met Hiroshi Mikitani, the CEO of Rakuten, while visiting Sendai accompanying Caroline on duties.[11]

In November 2013, Schlossberg attended the Medal of Freedom Award Dinner to commemorate the 50th anniversary of his grandfather's death where he introduced President Barack Obama.[13] Schlossberg is a member of the John F. Kennedy Library New Frontier Award Committee, for which he has acted as the award presenter.[14][15] He is on the committee of the Profile in Courage Award and was the host for the 2014 ceremony.[16]